Why I Changed My Mind About Multiple Products (And You Should Too)

For years, I preached single product focus. "Build one thing really well," I'd tell founders. Today, I'm running SimpleDirect with four product lines and ANC with three consulting verticals.

What changed? Everything. This episode breaks down why the season has shifted from single product focus to integrated ecosystems, and how AI fundamentally changed the competitive landscape.

Key Topics Covered

The Basecamp Revelation (2:30)

• Jason Fried's "to everything there is a season" insight
• Why Basecamp shut down everything in 2018, then launched four products in 2024
• Same founders, opposite strategies, both correct for their time

Personal Seasons Framework (6:15)

• Winter: Early/struggling, survival mode, single product essential
• Spring: Stable/growing, expanding into adjacencies
• Summer: Integrated/compounding, ecosystem approach
• Why you can move between seasons

The AI Market Shift (12:45)

• How product went from being the moat to easily replicable
• The 14-hour ChatGPT clone that changed everything
• Why technical complexity no longer protects you

Four Mental Shifts Required (18:30)

• Perfect product → Good enough + ship fast
• Single product → Integrated ecosystem
• Product-first → Content-first
• Anonymous builder → Personal brand

The Personal Seasons Breakdown

Winter Season (SimpleDirect 2019-2022):

• University of Waterloo, broke with co-founders
• Couldn't afford anything except making one product work
• Didn't pay themselves until 2022 profitability
• Single product focus was survival necessity

Summer Season (SimpleDirect 2023-Now):

• Cash flow from ANC consulting
• Scaled from 14 to 5 people using AI
• Have something to lose, playing defense
• Multiple products become strategic necessity

The Lesson: Different seasons require different strategies. What worked in winter kills you in summer, and vice versa.

The AI Wake-Up Call

The 14-Hour Development Story:

• Used Claude Coder to build ChatGPT competitor
• 14 total hours over two weeks, mostly watching AI code
• Built polished front-end and back-end platform
• Now using internally as SimpleDirect Chat

The Brutal Reality: If George can build sophisticated SaaS in 14 hours as non-programmer, anyone can replicate any product quickly.

Old Moat vs. New Moat:

• Old: Technical complexity, execution quality, compliance edge
• New: Distribution + trust + integrated ecosystem

The Four Mental Shifts

Shift 1: Perfect Product → Good Enough + Ship Fast

• Old Approach: Build perfect product, validate carefully, launch something people love
• New Approach: Ship scrappy product in two weeks, improve based on feedback
• Why: AI makes iteration cheap, perfection upfront is expensive and slow

Shift 2: Single Product → Integrated Ecosystem

• Example: Notion's evolution (Mail, Calendar, multiple products)
• Strategy: Build adjacent products solving different pain points for same customers
• Result: Even if they stop using one product, ecosystem keeps brand top-of-mind

Shift 3: Product-First → Content-First

• Old: Build amazing products, hope users find them
• New: Build audience first, product second
• Truth: Amazing product + no distribution = losing
• Example: Neobanking product got 1,000 users in 3 weeks through Product Hunt

Shift 4: Anonymous Builder → Personal Brand

• Reality: People remember people, not companies
• Strategy: Trust drives product adoption faster than features
• Investment: Time on Twitter, podcasts, newsletters (even though George prefers building)

Market Seasons vs. Personal Seasons

Pre-AI Market Season (1999-2022):

• Product was defensible moat
• Deep focus made competitive sense
• Technical complexity prevented copying
• Basecamp's 21-year single product success

AI Market Season (2023-Now):

• Products easily replicated with AI tools
• Distribution becomes critical differentiator
• Speed of iteration matters more than perfection
• Multiple products protect against commoditization

Real Examples and Numbers

SimpleDirect's Evolution:

• 2019-2022: Single product focus, broke to profitable
• 2023-Now: Four product lines plus ANC's three consulting verticals
• Used AI to scale productivity without hiring

Neobanking Case Study:

• 1,000 users in first three weeks
• Required bank account linking (not just signups)
• Success through Product Hunt and referral systems
• Product eventually failed but distribution proved viable

Current Reality:

• SimpleDirect: Four B2C product lines
• ANC: Three consulting verticals
• Content creation across multiple platforms
• Founder brand as competitive moat

Common Founder Blind Spots

Season Misalignment:

• Trying to diversify in winter season (survival mode)
• Staying single-product focused when market commoditizes your category
• Not recognizing when seasons change

Product Obsession:

• Believing better features automatically win
• Ignoring distribution until too late
• Underestimating speed of AI-enabled competition

False Binary Thinking:

• Assuming it's either single product OR multiple products
• Missing the timing element of strategic evolution
• Not adapting to market season changes

Quotable Moments

"To everything there is a season. Same founders, opposite strategies, both correct for their time.""If I can build a sophisticated SaaS product in 14 hours as a non-seasoned programmer, what does that mean for every other founder?""Product is no longer the moat. Your competitive advantage is people knowing you and trusting your founder journey.""The brutal truth: Amazing product + no distribution = losing.""I hate admitting this. I'm a product person. I want product quality to matter. But the season has changed.""Product differentiation is dying fast. Not dead, but dying.""Winter demands focus. Summer demands ecosystem. Know which season you're in."

Action Items for Different Seasons

If You're in Winter (Early/Struggling):

• Don't diversify yet - focus on one product
• Build until you have stable revenue and breathing room
• Document what you're learning for future expansion

If You're in Spring (Stable/Growing):

• Consider adjacent products for same customer base